Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/58—Preparation of carboxylic acid halides
  • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part

Definitions

• n is an integer of l to 6;
• n is an integer of2 to 6;
• R is hydrogen or alkyl
• each of R R R R, R and R is alkyl.
• alkyl refers to a straight or branched chain saturated aliphatic hydrocarbon group having a chain length of one to 12 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, n-hexyl, n-amyl, n-heptyl, noctyl, n-nonyl, lauryl, n-decyl, t-amyl, 3-ethylpentyl and 2- methylhexyl.
• the chain length of the alkyl group is one to six carbon atoms.
• the present invention provides a novel method for the control of insects which comprises treating the insects with an effective amount of a compound of formula A.
• a composition comprising an inert carrier and a compound of formula A.
• These compositions can be either liquid or solid.
• the exact formulation employed will vary according to factors, such as the specie of insect to be treated, the stage of the insects life at time of treatment, the degree or extent of insect infestation, environmental conditions and type of application.
• the most advantageous formulation (composition) for the control of a specific insect is determinable by those of ordinary skill in the art by routine experimentation giving due consideration to the foregoing factors and the description herein.
• the formulation employed is also dependent upon the primary role or mechanism of treating the insects that is, topical application (absorption), per oral application (ingestion), chemosterilant (sterility) or vaporization (inhalation).
• the primary mode of treating insects is, in turn, dependent on whether the insect is a chewing insect, a sucking insect or flying insect; whether the control of the insect is sought at the embryo, larvae, pupae or adult stage; and the locus of the insect.
• Formulations can be prepared by incorporating a compound of formula A with a solid inert carrier, such as finely divided talc, silica, pyrophyllite or clay or granular inert car riers, such as the vermiculites or a liquid inert .carrier, such as acetone, xylene, peanut oil, cottonseed oil, sesame oil and other vegetable and mineral oils conventionally employed as carriers in formulations for insect control.
• a solid inert carrier such as finely divided talc, silica, pyrophyllite or clay or granular inert car riers, such as the vermiculites or a liquid inert .carrier, such as acetone, xylene, peanut oil, cottonseed oil, sesame oil and other vegetable and mineral oils conventionally employed as carriers in formulations for insect control.
• Other components can be included, such at emulsifying agents, wetting agents and dispersing agents.
• the formulation will contain less than 95 percent
• control of insects by treating the insects with a compound of formula A is accomplished by the compounds ability to: inhibit metamorphosis; act as a direct insecticide, particularly at the embryo stage; act as a chemosterilant; or break the diapause of the insect.
• Treatment of insects by vapor action can be accomplished, for example, by formulating a compound of formula A with a resinous material, such as the vinyl polymers, e.g. polyvinyl chloride.
• a resinous material such as the vinyl polymers, e.g. polyvinyl chloride.
• This method is particularly useful for flying insects and treating enclosed areas. Suitable formulating method and carriers are described in U.S. Pat. No. 3,3l8,769, for example.
• Vapor effect and control through fumigation can also be done by spraying a solution which optionally contains a film-forming agent, such as wax, polyvinyl alcohol, or the like, onto structures.
• a film-forming agent such as wax, polyvinyl alcohol, or the like
• a second juvenile hormone from the same source has been identified as methyl l0,l l-oxido-3,7,l l-trimethyltrideca-2,6- dienoate by Meyer et al., The Two Juvenile Hormones from the Cecropia Silk Moth", Zoology (Proc. N.A.S.) 60, 853 (1968).
• some synthetic terpenoids have been reported exhibiting maturation inhibiting, sterility or ovicidal activity.
• the trans isomer is preferably employed for the control of insects.
• Typical insects which can be controlled by treatment with a compound of formula A in accordance with the present invention are Dysdercus cingluatus, Tenebrio molitor, Galleria mellonella, Tribolium confusum, Periplanera Americana, Hypera puctata (clover leaf weevil), Dysdercus suturellus, Aphididae, such as melon aphid and cabbage aphid, Tinea pellionella, Silophilus granarius, Lygus hesperus, Schistocerca yoga and Pyrrhocoris aplerus.
• each of R', R R", R, R R, m and n is as defined hereinabove.
• an acyl chloride or bromide of formula I is reacted with anhydrous hydrogen fluoride at a temperature of from about room temperature to 10 C.
• reaction is generally complete in from a few minutes to a few hours, such as about 30 minutes to 2 hours.
• a solvent inert such as ether, tetrahydrofuran, benzene, toluene, hexane, pentane, and the like.
• EXAMPLE 1 A. One gram of thionyl chloride is added with stirring at room temperature to 0.5 g. of 3,7,7,1 1,1 l-pentamethyldodec- 2-enoic acid in benzene and stirred at about room temperature for about 2 hours. Excess thionyl chloride is removed by evaporation and the solvent evaporated under reduced pressure to yield the acid chloride (3,7,1 l,l l-pentamethyldodec- 2-enyl chloride).
• the acyl bromide is prepared using phosphorus pentabromide and temperature of about 35 for 2 hours.
• EXAMPLE 2 lnto 10 g. of 3,7,7,l l,l 1-pentamethyldodec-2-enoyl chloride, at 5 to 0, a continuous stream of anhydrous gaseous hydrogen fluoride is introduced slowly for about l hour. The reaction is then allowed to warm to room temperature and stand for 2 hours. Excess hydrogen fluoride is removed by addition of dry sodium fluoride and then the mixture filtered. The filtrate is purified by chromatography or distillation to yield 3,7,7,1 1,1 l-pentamethyldodec-2-enoyl fluoride.
• the above reaction can also be carried out by adding the required amount (1 molar equivalent or slight excess) of anhydrous liquid hydrogen fluoride to 3,7,7,1 l,l l-pentamethyldodec-2-enoyl chloride at 5 to 0 with stirring.
• each of the acyl chlorides of Example 1 (Part A) is converted into the corresponding acyl fluoride, that is:
• EXAMPLE 3 Compositions suitable for the control of insects in accordance with the present invention are exemplified by the following. Parts by weight.
• n is an integer of l to 6;
• n is an integer of 2 to 6;
• R is hydrogen or alkyl containing from one to six carbon atoms
• each of R, R, R, R and R is alkyl containing from one to six carbon atoms.
• each of R, R, R and R is methyl and each of R and R is ethyl.
• each of R, R, R and R is methyl and R is methyl or ethyl.
• each of R, R and R is methyl and each of R and R is ethyl.
• n is an integer of l to 6; R is hydrogen or alkyl containing from one to six carbon atoms; and each of R, R, R, R and R is alkyl containing from one to six carbon atoms. 15. A compound according to claim 14 wherein each of R, R R, R and R is methyl or ethyl and R is hydrogen, methyl 10 or ethyl.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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Cited By (2)

• 1970
  • 1970-02-26 US US14660A patent/US3679720A/en not_active Expired - Lifetime
• 1971
  • 1971-02-22 NL NL7102308A patent/NL7102308A/xx unknown
  • 1971-02-22 AU AU25710/71A patent/AU2571071A/en not_active Expired
  • 1971-02-23 FR FR7106145A patent/FR2078972A5/fr not_active Expired
  • 1971-02-23 DE DE19712108576 patent/DE2108576A1/de active Pending

Non-Patent Citations (3)

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